Surface-active hydroxysulfonates

Abstract

Aqueous solutions of surface-active hydroxysulfonates are obtained by reaction of unsaturated fatty alkenyl or fatty alkenyl polyalkoxyl esters, for example of oleyl acetate or oleyl polyethoxyl acetate, with sulfur trioxide, introduction of the reaction product into aqueous alkali metal, alkaline-earth or ammonium hydroxide and heating of the solutions until the ester and sultone groups present have been hydrolyzed.

We claim: 
     
       1. A process for the production of an aqueous solution of an alkali metal alkaline-earth or ammonium salt of a surface-active hydroxysulfonate, comprising reacting with gaseous sulfur trioxide at a temperature of 10° to about 80° C. an unsaturated fatty alkenyl or fatty alkenyl polyalkoxyl ester corresponding to formula (I) ##STR3## in which R 1  is a linear C 16  -C 22  alkenyl group or a fatty hydrocarbon group consisting essentially of an oleyl, palmitoleyl, linoleyl, gadoleyl or erucyl group, n is a number from 2 to 4, x=0 or is a number up to 30, and R 2  --CO is a C 1  -C 4  acyl group; introducing the reaction product into an aqueous solution of about 1 to about 2.5 mol of alkali metal, alkaline-earth or ammonium hydroxide per mol of added SO 3  ; and heating the solution until the ester and sultone groups present have been hydrolyzed. 
     
     
       2. A process as in claim 1 wherein n=2, and x=0 or is a number up to 10. 
     
     
       3. A process as in claim 1 wherein R 2  --CO is a formyl, acetyl, propionyl or butyryl group. 
     
     
       4. A process as in claim 1 wherein the reaction with sulfur trioxide is carried out at a temperature of about 20° to about 50° C. with a mixture of SO 3  and air or an inert gas containing about 1 to about 10% by volume of SO 3 . 
     
     
       5. A process as in claim 1 wherein R 1  is an oleyl group or a fatty hydrocarbon radical consisting essentially of oleyl groups. 
     
     
       6. A process as in claim 1 including recovering a mixture of surface-active hydroxysulfonates consisting essentially of compounds corresponding to formula (II) or (III) ##STR4## in which y and z=0 or a number from 1 to 18, p=0, 1 or 2 and the sum of (y+z+p) is a number from 12 to 18 and x=0 or is a number up to 30 and n is an integer from 2 to 4, or an alkali metal, alkaline-earth or ammonium salt thereof. 
     
     
       7. An aqueous solution of an alkali metal, alkaline-earth or ammonium salt of a surface-active hydroxysulfonate prepared by the process comprising reacting with gaseous sulfur trioxide at a temperature of 10° to about 80° C. an unsaturaed fatty alkenyl or fatty alkenyl polyalkoxyl ester corresponding to formula (I) ##STR5## in which R 1  is a linear C 16  -C 22  alkenyl group or a fatty hydrocarbon group consisting essentially of an oleyl, palmitoleyl, linoleyl, gadoleyl or erucyl group, n is a number from 2 to 4, x=0 or is a number up to 30, and R 2  --CO is a C 1  -C 4  acyl group; introducing the reaction product into an aqueous solution of about 1 to about 2.5 mol of alkali metal, alkaline-earth or ammonium hydroxide per mol of added SO 3  ; and heating the solution until the ester and sultone groups present have been hydrolyzed. 
     
     
       8. An aqueous solution as in claim 7 wherein n=2, and x=0 or is a number up to 10. 
     
     
       9. An aqueous solution as in claim 7 wherein R 2  --CO is a formyl, acetyl, propionyl or butyryl group. 
     
     
       10. An aqueous solution as in claim 7 wherein the reaction with sulfur trioxide is carried out at a temperature of about 20° to about 50° C. with a mixture of SO 3  and air or an inert gas containing about 1 to about 10% by volume of SO 3 . 
     
     
       11. An aqueous solution as in claim 7 wherein R 1  is an oleyl group or a fatty alkyl radical consisting essentially of oleyl groups. 
     
     
       12. An aqueous solution as in claim 7 comprising a mixture of surfaceactive hydroxysulfonates consisting essentially of compounds corresponding to formula (II) or (III) ##STR6## in which y and z=0 or a number from 1 to 18, p=0, 1 or 2 and the sum of (y+z+p) is a number from 12 to 18 and x=0 or is a number up to 30 and n is an integer from 2 to 4, or an alkali metal, alkaline-earth or ammonium salt thereof. 
     
     
       13. The process of preparing a cleaning composition comprising adding thereto an alkali metal, alkaline-earth or ammonium salt of a surface-active hydroxysulfonate prepared by the process comprising reacting with gaseous sulfur trioxide at a temperature of 10° to about 80° C. an unsaturated fatty alkenyl or fatty alkenyl polyalkoxyl ester corresponding to formula (I) ##STR7## in which R 1  is a linear C 16  -C 22  alkenyl group or a fatty hydrocarbon group consisting essentially of an oleyl, palmitoleyl, linoleyl, gadoleyl or erucyl group, n is a number from 2 to 4, x=0 or is a number up to 30, and R 2  --CO is a C 1  -C 4  acyl group; introducing the reaction product into an aqueous solution of about 1 to about 2.5 mol of alkali metal, alkaline-earth or ammonium hydroxide per mol of added SO 3  ; and heating the solution until the ester and sultone groups present have been hydrolyzed. 
     
     
       14. The process as in claim 13 wherein n=2, and x=0 or is a number up to 10. 
     
     
       15. The process as in claim 13 wherein R 2  --CO is a formyl, acetyl, propionyl or butyryl group. 
     
     
       16. The process as in claim 13 wherein the reaction with sulfur trioxide is carried out at a temperature of about 20° to about 50° C. with a mixture of SO 3  and air or an inert gas containing about 1 to about 10% by volume of SO 3 . 
     
     
       17. The process as in claim 13 wherein R 1  is an oleyl group or a fatty hydrocarbon radical consisting essentially of oleyl groups. 
     
     
       18. The process as in claim 13 wherein said hydroxysulfonate comprises a mixture of surface-active hydroxysulfonates consisting essentially of compounds corresponding to formula (II) or (III) ##STR8## in which y and z=0 or a number from 1 to 18, p=0, 1 or 2 and the sum of (y+z+p) is a number from 12 to 18 and x=0 or is a number up to 30 and n is an integer from 2 to 4, or an alkali metal, alkaline-earth or ammonium salt thereof.